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Cuba, Hispaniola and Jamaica range from 40,852 square miles to 4,320 square miles in land area. Cuba is the biggest. Hispaniola is the second biggest at 29,529 square miles while Jamaica is the smallest of the three. It is worth noting that Puerto Rico's sovereign area, including water, is 5,324 square miles, larger than that of Jamaica. However, Jamaica is larger than Puerto Rico when taking only land mass into account.

Because of its large size, Hispaniola accommodates two nation-states, that of Haiti and the Dominican Republic. These two nation-states are also the second- and third-largest nations by population. As of 2011, Cuba is the largest with a population of 11,241,161 people. Haiti's population is 9,993,247 people. The population of the Dominican Republic is 9,445,281 people. Cuba, Haiti and the Dominican Republic each accommodate about 25 percent of the population of the Caribbean.

Despite Puerto Rico having a smaller land area than Jamaica, Puerto Rico boasts a larger population of 3,641,000 people compared to Jamaica's 2,715,000.